Tobey Maguire Poker Story: Discover the Complete Molly’s Game Backstory

Home » Tobey Maguire Poker Story: Discover the Complete Molly’s Game Backstory

Some may find it surprising, yet some prominent celebrities are well-known for being avid gamblers.

Tobey Maguire, who plays Spiderman, was one of the celebrities accused of conducting illegal high-stakes poker games in 2011. Usually, celebrities keep their gambling affairs under wraps, but this particular case was blown thanks to the memoir “Molly’s Game” by Molly Bloom. 

In the memoir, Molly revealed that the “friendly neighborhood Spiderman” actor had a rather unpleasant personality. The book exposed the private games she hosted for A-list Hollywood celebrities and was later adapted as a movie. Unfortunately for Tobey, it showed the world that he was rude and arrogant, which curtailed his career in the movie industry.

The whole story is rather intriguing, and we’ll cover it all in this article.

Tobey Maguire’s Poker Skill

Although Tobey Maguire doesn’t look it, he’s good at poker and has made a fortune from playing poker. For most Hollywood actors, the breaks between productions were enough to pick up several vices like playing online casino games like; poker, slots, blackjack, and sports betting, and Tobey’s case was no different. 

Out of all the activities to try out, he chose casino gambling and developed a high level of interest in poker. Tobey loved poker so much that he even took part in it. His addiction pushed him to participate in the World Series of Poker Competition in 2011, where he won the Players Championship title. 

At that time, he frequented some top casinos often to play the game, but his winnings didn’t seem enough for him; he wanted more. He continued beating more prominent names and cashing out massively but still didn’t want to leave the tables. He even started hosting poker games in his home alongside his good friend Houston Curtis and his ex-wife, Jen Meyer. Tobey later moved the game location to the Viper Room nightclub, where he and Curtis met Molly. 

The Creation Of The Underground Poker Game Ring

The wheel was set in place after Molly crashed horribly during an Olympic qualifying run and had to give it up. Molly moved to Los Angeles, where she met her new boss, Darin Feinstein. He was the manager of a nightclub called The Viper and asked her to work there as a waitress and also his assistant. 

Darin later introduced her to the poker world and asked her to help him manage the casino game. Molly soon became familiar with poker and met with several billionaires and A-list actors, including Tobey and Curtis. On her first night on the task, Molly made a whopping $3,000 in tips, further spiking her interest in the game. Her boss fired her after seeing how much control she had over the game.

After she was fired, Molly met with Tobey and Curtis, and they decided to launch their gambling party. Tobey brought the idea of using Molly’s connections from her former job to gather A-list actors and billionaires.

Molly started organizing the high-stakes game every Tuesday, and things ran smoothly. She made players feel comfortable throughout their stay while she served drinks and collected tips. Wealthy people kept showing up and losing their fortunes, and Molly, Tobey, and Curtis were on a winning spree.

The ring was constantly frequented by top influential people and big stars like Ben Affleck, Leonardo DiCaprio, Pete Sampras, Matt Damon, and many others. Tobey frequently used these actors to add glamour to the setup, while Molly deflected attention from Tobey and Curtis.

Molly Bloom and the Molly’s Game Memoir

The story gets more interesting after the memoir “Molly’s Game” was released by Molly.

According to what she wrote in the book, Tobey wasn’t a regular poker player. He had an evil personality and used his skills to his advantage. It was also revealed that Tobey particularly targeted rich Hollywood stars, and in his words, he wanted to “help rid them of some of that excess wealth.”

Tobey and Curtis raked in so much money from the games and enlisted Leo DiCaprio as a lure. They didn’t even have to cheat because Tobey was a far better player than most people who frequented the place.

It soon got to a point when Tobey became jealous of the money she made from her tips. Molly took as much as $30,000 in tips home every game night, which didn’t sit well with Tobey. He felt the whole thing was centered around him, and she was making way more than she deserved. According to her, during the games, the actor was ” the best player, the worst tipper, and the absolute worst loser.”

She recorded that the actor humiliated her in front of other players by asking her to bark like a seal to receive a $1,000 tip. She refused to do it, and Tobey stormed off angrily. This caused animosity between them, and before long, Tobey moved the game venue and proceeded to cut off Molly completely. Determined, Molly also created her poker party, and things ran smoothly until she was involved in illegal practices. 

Molly’s Game: What Does The Movie Say? 

Molly's Game: one of the best poker films

The Molly’s Game memoir was published in 2014; following that, a movie version was made and released in 2017. The movie follows the story of Molly Bloom, played by the actress Jessica Chastain, and the character Player X.

In the movie, Player X and his friends leave Molly’s former boss’s nightclub to play at Molly’s new poker party. While her move was successful, Player X kept pressuring her to raise the stakes so they could make more money. Molly later discovers that Player X enjoyed ruining people’s lives, and soon, they have a falling out. He later switches the venue and leaves Molly behind, to her dismay. 

Undeterred, she moves to NYC to start up her poker ring and is later convinced to carry out some illegal operations. Things started falling apart when one of her players, Brad, was caught due to his involvement in a Ponzi scheme. She is later investigated and then sentenced to court.

The film is currently among the most well-liked poker movies ever.

Tobey Maguire as the Famous Molly’s Game “Player X”

A couple of celebrities who frequented Molly Bloom’s underground poker games were first exposed in the media before the release of her memoir. However, there was still speculation on who the Player X character was as portrayed in the real-life movie “Molly’s Game.”

The film director, Aaron Sorkin, didn’t name the celebrities that frequented the underground poker events in his film. However, Molly Bloom made these personalities known, as mentioned in her memoir.

According to Molly Bloom, regulars of illegal gambling included A-listers like Alez Rodriguez, Ben Affleck, Leonardo DiCaprio, and Tobey Maguire. Therefore, it is obvious that viewers are curious about the identity of Player X. This character is portrayed by none other than the famous Tobey Maguire, as seen in the Memoir.

Tobey Maguire, who plays the role of Spider-Man, is a frequent winner in high-stakes poker tournaments, according to Molly. The Player X character, played by Michael Cera in the film, was an evil personality who delighted in ruining the lives of his fellow players.

As a result, the fictional character “Player X” portrayed the actions of Tobey Maguire as written by Bloom in her Molly’s Game. According to the movie and book, Tobey depicted the following characters:

A Stone-Cold Bluff

According to the memoir and the film, Maguire is a stone-cold bluff who takes advantage of his opponents’ trust. Being an actor makes him very convincing, too.

Greed and Obsession 

Also mentioned in Molly’s Game book is Maguire cutting out an over-deal to cover Houston Curtis’ loss during a devastating hand. According to Bloom, the Spiderman actor agreed to cover Curtis’ losses for 50% of the television producer’s wins until the debt is paid off.

Also, according to Molly Bloom, over time, Tobey Maguire became obsessed with her earnings from tips and growing influence. He wasn’t happy about her role and kept nagging her about it.

Changing the Underground Poker Games Venue to cut off Bloom

Still obsessed with her tips and growing influence, Tobey Maguire influenced the change of the underground poker venue. According to Bloom, the American actor had organized a different venue from the one she had prepared and informed her that her services were no longer required. 

It Wasn’t Molly’s Game After All, But Tobey Maguire’s

Although the movie and memoir were centered around Bloom’s character, they also exposed Tobey Maguire. As a result, it seems like the Spider-Man actor was the moving force behind the underground poker games. 

While Bloom’s major concern was making an income for herself through the tips, Maguire was focused on increasing his bankroll.

According to Molly, the actor had stated that he intended to make $10 million from poker. Tobey is said to have made a huge sum from the illegal gambling games before it was brought to light.

Tobey Maguire Lawsuits and Legal Consequences Over Illegal Poker Games

Tobey Maguire Gambling Stories You Won't Believe Are True

Similar to U.S. Senators questioning Binance’s transparency, in March 2011, Maguire was served a massive civil lawsuit by Ruderman Capital Partners in the U.S. Bankruptcy Court. The lawsuit alleged that the Spider-Man actor had won $311,000 from Bradley Ruderman in various poker games. $110,000 of that sum was won during a single-hand match in 2007. 

According to the lawsuit, Ruderman had allegedly organized a Ponzi scheme, taking over $44 million from a group of 22 investors. The victims’ funds were obtained under the pretense of investing them. However, the businessman used the money to cover his gambling losses.

The hedge-fund manager used some of the ill-gotten funds to play in the poker games organized by Tobey. However, he lost a chunk of it to the Spider-Man actor. In the complaint issued by the group of investors, the $311,300 won by Maguire from Bradley was to be returned.

The profits were allegedly obtained dishonestly through illicit games, thus the actor was required to return them, according to the investors. The lawsuit further stated that the poker games were unlicensed and illegal. Therefore, the actor had no legal right to receive payment.

Several other regulars of the poker games were brought in as defendants in the lawsuit. This includes actors Nick Cassavetes and Gabe Kaplan,  professional poker player Dan Bilzerian, a Los Angeles lawyer, and two nightclub owners.

Toby Maguire and the other defendants in the civil lawsuits didn’t face any criminal charges. Nevertheless, they were ordered to refund a minimum of $1.5 million of their purported gambling earnings by the bankruptcy trustee for Ruderman’s estate. Each defendant had beaten Ruderman in high-stakes poker games.

Maguire agreed to pay the sum of $80,000 to settle the lawsuit. Ruderman’s estate received the sum as part of an agreement. Bradley Ruderman, in turn, was asked to pay $1.5 million as compensation to the scammed investors. A ten-year jail term for his participation in the Ponzi scam was imposed after that.

Other regulars of the Maguire Poker sessions were not left out of the lawsuit. Bilzerian was sued for $100,000. Gabe Kaplan also paid the sum of $27,000 as a settlement. Molly wasn’t left out because she was sued for $473,200 for her involvement in the game’s origin.

Later, she was detained and given a probationary period of one year. Also, she forfeited her earnings from the sessions, approximately $125,000.

Tobey Maguire’s Life Today: Does He Still Gamble?

American actor Tobey Maguire must have been an elite-level poker player to win that huge amount of money from poker games. Following the revelation of the gambling ring, there have been concerns over the famous Spider-Man actor having a gambling addiction.

However, the truth about this fear may never be known. Tobey has chosen to live a quiet life away from the media and spotlight following the illegal poker game incidents. As a result, he no longer plays poker games or gambles. The actor had chosen to stay away from the game completely.

He is said to be focused on film production, where he finances small movies and makes cameo appearances in a couple of movies.

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